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Volumn 42, Issue 44, 2003, Pages 5394-5399

Novel Substrates for Palladium-Catalyzed Coupling Reactions of Arenes

Author keywords

Carbonic acids; Cross coupling; Homogeneous catalysis; Ketones; Palladium

Indexed keywords

CATALYSIS; PALLADIUM; TRANSITION METALS;

EID: 0345276540     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200301681     Document Type: Short Survey
Times cited : (88)

References (73)
  • 1
    • 0003779363 scopus 로고    scopus 로고
    • (Eds.: M. Beller, C. Bolm), Wiley-VCH, Weinheim
    • a) Transition Metals for Organic Synthesis (Eds.: M. Beller, C. Bolm), Wiley-VCH, Weinheim, 1998;
    • (1998) Transition Metals for Organic Synthesis
  • 2
    • 0003748614 scopus 로고    scopus 로고
    • (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim
    • b) Metal-catalyzed Crosscoupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998.
    • (1998) Metal-catalyzed Crosscoupling Reactions
  • 6
    • 0000261434 scopus 로고    scopus 로고
    • a) L. Botella, C. Nájera, Angew. Chem. 2002, 114, 187-189; Angew. Chem. Int. Ed. 2002, 41, 179-181;
    • (2002) Angew. Chem. , vol.114 , pp. 187-189
    • Botella, L.1    Nájera, C.2
  • 7
    • 0037016464 scopus 로고    scopus 로고
    • a) L. Botella, C. Nájera, Angew. Chem. 2002, 114, 187-189; Angew. Chem. Int. Ed. 2002, 41, 179-181;
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 179-181
  • 10
    • 0034680642 scopus 로고    scopus 로고
    • c) A. Zapf, A. Ehrentraut, M. Beller, Angew. Chem. 2000, 112, 4315-4317; Angew. Chem. Int. Ed. 2000, 39, 4153-4155;
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 4153-4155
  • 12
    • 0000447504 scopus 로고    scopus 로고
    • e) J. P. Wolfe, S. L. Buchwald, Angew. Chem. 1999, 111, 2570-2573; Angew. Chem. Int. Ed. 1999, 38, 2413-2416;
    • (1999) Angew. Chem. , vol.111 , pp. 2570-2573
    • Wolfe, J.P.1    Buchwald, S.L.2
  • 13
    • 0033549829 scopus 로고    scopus 로고
    • e) J. P. Wolfe, S. L. Buchwald, Angew. Chem. 1999, 111, 2570-2573; Angew. Chem. Int. Ed. 1999, 38, 2413-2416;
    • (1999) Angew. Chem. Int. Ed. , vol.38 , pp. 2413-2416
  • 15
    • 33748233333 scopus 로고
    • f) M. Beller, H. Fischer, W. A. Herrmann, K. Öfele, C. Broßmer, Angew. Chem. 1995, 107, 1992-1993; Angew. Chem. Int. Ed. Engl. 1995, 34, 1848-1849.
    • (1995) Angew. Chem. Int. Ed. Engl. , vol.34 , pp. 1848-1849
  • 16
    • 0001075235 scopus 로고    scopus 로고
    • W. A. Herrmann, Angew. Chem. 2002, 114, 1342-1363; Angew. Chem. Int. Ed. 2002, 41, 1290-1309.
    • (2002) Angew. Chem. , vol.114 , pp. 1342-1363
    • Herrmann, W.A.1
  • 17
    • 0037090932 scopus 로고    scopus 로고
    • W. A. Herrmann, Angew. Chem. 2002, 114, 1342-1363; Angew. Chem. Int. Ed. 2002, 41, 1290-1309.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 1290-1309
  • 18
    • 0001108788 scopus 로고    scopus 로고
    • G. Dyker, Angew. Chem. 1999, 111, 1808-1822; Angew. Chem. Int. Ed. 1999, 38, 1699-1712.
    • (1999) Angew. Chem. , vol.111 , pp. 1808-1822
    • Dyker, G.1
  • 19
    • 0033553817 scopus 로고    scopus 로고
    • G. Dyker, Angew. Chem. 1999, 111, 1808-1822; Angew. Chem. Int. Ed. 1999, 38, 1699-1712.
    • (1999) Angew. Chem. Int. Ed. , vol.38 , pp. 1699-1712
  • 20
    • 0033118177 scopus 로고    scopus 로고
    • Review: R. K. Dieter, Tetrahedron 1999, 55, 4177-4236.
    • (1999) Tetrahedron , vol.55 , pp. 4177-4236
    • Dieter, R.K.1
  • 33
    • 0027373967 scopus 로고
    • 4] to yield phenyl pyridyl ketones could be the first published coupling reaction of an anhydride. However, the authors did not compare the results with a Pd-free system, and the yields were <40%: T. Sakamoto, Y. Kondo, N. Murata, H. Yamanaka, Tetrahedron 1993, 49, 9713-9720.
    • (1993) Tetrahedron , vol.49 , pp. 9713-9720
    • Sakamoto, T.1    Kondo, Y.2    Murata, N.3    Yamanaka, H.4
  • 35
    • 0031925015 scopus 로고    scopus 로고
    • a) M. S. Stephan, A. J. J. M. Teunissen, G. K. M. Verzijl, J. G. de Vries, Angew. Chem. 1998, 110, 688-690; Angew. Chem. Int. Ed. 1998, 37, 662-664;
    • (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 662-664
  • 36
    • 0344613618 scopus 로고    scopus 로고
    • Catalysis of Organic Reactions
    • "Catalysis of Organic Reactions": M. S. Stephan, J. G. de Vries, Chem. Ind. 2001, 82, 379-390.
    • (2001) Chem. Ind. , vol.82 , pp. 379-390
    • Stephan, M.S.1    De Vries, J.G.2
  • 43
  • 44
    • 0037006837 scopus 로고    scopus 로고
    • L. J. Gooßen, J. Paetzold, Angew. Chem. 2002, 114, 1285-1289; Angew. Chem. Int. Ed. 2002, 41, 1237-1241.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 1237-1241
  • 48
    • 4243728992 scopus 로고    scopus 로고
    • a) L. J. Gooßen, K. Gosh, Angew. Chem. 2001, 113, 3566-3568; Angew. Chem. Int. Ed. 2001, 40, 3458-3460;
    • (2001) Angew. Chem. , vol.113 , pp. 3566-3568
    • Gooßen, L.J.1    Gosh, K.2
  • 49
    • 0035903581 scopus 로고    scopus 로고
    • a) L. J. Gooßen, K. Gosh, Angew. Chem. 2001, 113, 3566-3568; Angew. Chem. Int. Ed. 2001, 40, 3458-3460;
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 3458-3460
  • 56
    • 0001920234 scopus 로고
    • The coupling of allyl sulfides with Ni or Pd catalysts has already been known for some time: H. Okamura, J. Takei, Tetrahedron Lett. 1979, 3425-3428.
    • (1979) Tetrahedron Lett. , pp. 3425-3428
    • Okamura, H.1    Takei, J.2
  • 57
    • 0033574612 scopus 로고    scopus 로고
    • J. Srogl, G. D. Allred, L. S. Liebeskind, J. Am. Chem. Soc. 1997, 119, 12376-12377. S-Benzylsulfonium salts are more reactive than the corresponding aryl derivatives and can also be coupled with organotin or -zinc reagents; see: S. Zhang, D. Marshall, L. S. Liebeskind, J. Org. Chem. 1999, 64, 2796-2804.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 12376-12377
    • Srogl, J.1    Allred, G.D.2    Liebeskind, L.S.3
  • 58
    • 0033574612 scopus 로고    scopus 로고
    • J. Srogl, G. D. Allred, L. S. Liebeskind, J. Am. Chem. Soc. 1997, 119, 12376-12377. S-Benzylsulfonium salts are more reactive than the corresponding aryl derivatives and can also be coupled with organotin or -zinc reagents; see: S. Zhang, D. Marshall, L. S. Liebeskind, J. Org. Chem. 1999, 64, 2796-2804.
    • (1999) J. Org. Chem. , vol.64 , pp. 2796-2804
    • Zhang, S.1    Marshall, D.2    Liebeskind, L.S.3
  • 62
    • 0001261319 scopus 로고    scopus 로고
    • A "simple" coupling of aryl thiol esters with aryl boronic acids has only been described as a side reaction in the Suzuki coupling of acyl thiophenyl bromides: B. Zeysing, C. Gosch, A. Terfort. Org. Lett. 2000, 2, 1843-1845.
    • (2000) Org. Lett. , vol.2 , pp. 1843-1845
    • Zeysing, B.1    Gosch, C.2    Terfort, A.3
  • 63
    • 0034669524 scopus 로고    scopus 로고
    • L. S. Liebeskind, J. Srogl, J. Am. Chem. Soc. 2000, 122, 11260-11261. In the same way alkynyl thioethers can be coupled to aryl acetylenes (C. Savarin, J. Srogl, L. S. Liebeskind, Org. Lett. 2001, 3, 91-93) as well as methylthiopseudoureas to aryl amidines (C. L. Kusturin, L. S. Liebeskind, W. L. Neumann, Org. Lett. 2002, 4, 983-985).
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 11260-11261
    • Liebeskind, L.S.1    Srogl, J.2
  • 64
    • 0035843313 scopus 로고    scopus 로고
    • L. S. Liebeskind, J. Srogl, J. Am. Chem. Soc. 2000, 122, 11260-11261. In the same way alkynyl thioethers can be coupled to aryl acetylenes (C. Savarin, J. Srogl, L. S. Liebeskind, Org. Lett. 2001, 3, 91-93) as well as methylthiopseudoureas to aryl amidines (C. L. Kusturin, L. S. Liebeskind, W. L. Neumann, Org. Lett. 2002, 4, 983-985).
    • (2001) Org. Lett. , vol.3 , pp. 91-93
    • Savarin, C.1    Srogl, J.2    Liebeskind, L.S.3
  • 65
    • 0012215670 scopus 로고    scopus 로고
    • L. S. Liebeskind, J. Srogl, J. Am. Chem. Soc. 2000, 122, 11260-11261. In the same way alkynyl thioethers can be coupled to aryl acetylenes (C. Savarin, J. Srogl, L. S. Liebeskind, Org. Lett. 2001, 3, 91-93) as well as methylthiopseudoureas to aryl amidines (C. L. Kusturin, L. S. Liebeskind, W. L. Neumann, Org. Lett. 2002, 4, 983-985).
    • (2002) Org. Lett. , vol.4 , pp. 983-985
    • Kusturin, C.L.1    Liebeskind, L.S.2    Neumann, W.L.3
  • 71
    • 0035903607 scopus 로고    scopus 로고
    • NAr mechanism, see: Y. M. Kim, S. Yu, J. Am. Chem. Soc. 2003, 125, 1696-1697.
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 3387-3389


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